This project concerns the biogenesis of slaframine (1) and a pyrindine alkaloid (2) from pipecolic acid in Rhizoctonia leguminicola. Isotope data have established (5) and (6) as intermediates in (1) biosynthesis. Work will continue on possible routes for functionalization of the 6-position of (1) particularly by tracing pipecolic acid, labeled variously with deuterium into biosynthesized (1). A new synthesis of (1) from 1-hydroxyoctahydroindolizines is being developed, a key aspect being the control of relative configurations of the three asymmetric centers. A study of the synthesis of 3-hydroxy-l-oxooctahydroindolizine, a possible first intermediate in the biosynthetic pathway to have the complete indolizine nucleus, is being undertaken. Work will continue on accumulating (1) and (2) needed for subsequent biological and chemical studies, and to delineate certain of the enzymatic transformations implied in the scheme. This project summary contained formulas, drawings, tables or nonkeyable data which are not shown above.